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Chemical Synthesis and Sequencing of Peptides and Proteins, Lui, T.

The Fmoc Group

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In organic chemistry, peptide synthesis is the ..

In Fmoc solid-phase peptide synthesis, the peptide chain is assembled stepwise, one amino acid at a time, while attached to an insoluble resin support. This allows the reaction by-products to be removed at each step by simple washing. Amino acids are protected at their amino terminus by the Fmoc (9-fluorenylmethoxycarbonyl) group and coupled to the growing chain after activation of the carboxylic acid terminus. The Fmoc group is then removed by piperidine treatment and the process repeated. After the peptide has been assembled it is removed from the resin by treatment with trifluoroacetic acid (TFA). At the same time, protecting groups on amino acid side chains are also removed yielding the crude linear peptide. One-step purification by reverse-phase HPLC is often sufficient to obtain the peptide in >95% purity.

The general scheme for solid phase peptide synthesis is outlined in Figure 1.

Immobilize your newly synthesized peptides without changing the tag. The unique properties of fluorous compounds allow them to be immobilized onto fluorous-modified surfaces in the formation of microarrays. To date, small molecules, peptides, and carbohydrate arrays have all been formed using fluorous immobilization. Read more about fluorous peptide microarrays .

Chemistry of Peptide Synthesis - CRC Press Book

The second Fmoc amino acid is coupled utilizing a pre-activated species or in situ activation.

This formation is likely to occur with all but the shortest of peptides and is even more pronounced in peptides containing multiple hydrophobic amino acid residues.

A range of cleavage reagents for peptides synthesized on 2-chlorotrityl resin has been described. TFE/AcOH/DCM (1:1:3) has been developed by Barbs [62]. Cleavage is also rapidly attained with 0.5% TFA/DCM as well as with HFIP/DCM (1:4 or 3:7) [63].

Solid Phase Peptide Synthesis : The Basics - YouTube

The removal of peptides in solid phase peptide synthesis is primarily done by acidolysis.

Two major chemistries for solid phase peptide synthesis are Fmoc (base labile protecting group) and t-Boc (acid labile a-amino protecting group). Each method involves fundamentally different amino acid side-chain protection and consequent cleavage/deprotection methods, and resins; t-Boc method requires use of stronger HF containing anisole alone or anisole plus other scavengers, where peptide-resins assembled by Fmoc chemistry usually cleaved by less harsh Reagents K or R. Fmoc chemistry is known for peptide synthesis of higher quality and in greater yield than t-Boc chemistry. Impurities in t-Boc-synthesized peptides mostly attributed to cleavage problems, dehydration and t-butylation. For peptide assembly HBTU/HOBt, carbodiimide-mediated coupling and PyBOP/HOBt are the most popular routines. Peptides usually purified by reversed-phase HPLC (high performance liquid chromatography) using columns such as C-18, C-8, and C-4.

For large scale synthesis of well known peptides solution or liquid phase peptide synthesis can be applied. These "classical" methods for synthesis in solution are labour, time, and skill intensive largely due to the unpredictable solubility characteristics of intermediates.

The Fmoc chemistry employs the use of weak acids such as TFA or TMSBr.
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  • Overview of Peptide Synthesis - AnaSpec

    Initially, the first Fmoc amino acid is attached to an insoluble support resin via an acid labile linker.

  • Fmoc solid-phase synthesis - CRB Discovery

    Deprotection of Fmoc, is accomplished by treatment of the amino acid with a base, usually piperidine.

  • Solid Phase Peptide Synthesis : The Basics ..

    Attempts at incorporating symmetrical anhydrides to Fmoc amino acids were met with some difficulties (34-36).

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Fmoc-Chemistry for Peptide Synthesis.

A recent publication has described the in situ preparation of Fmoc amino acid chlorides by reaction with bis(trichloromethyl) carbonate and their use in difficult couplings [36].

Synthesis of chiral peptide nucleic acids ..

Fmoc amino acid chlorides can also be used but their applicability is more limited [33]; also acid-sensitive groups may not be present when treating Fmoc amino acids with oxalyl chloride or thionyl chloride to obtain the acid chlorides [34,35].

Advances in Fmoc solid-phase peptide synthesis - …

Also small scale manual SPPS as well as multiple peptide synthesis and the synthesis of pep- tide libraries can be performed very rapidly and conveniently with preformed active esters. Fmoc-AA-ONp and Fmoc-AA-OSu have found only restricted application in SPPS.

Advances in Fmoc solid-phase peptide ..

The same is true for the activation of Fmoc-His(Trt)-OH since racemization catalyzed by the nitrogen of the imidazole ring may occur. For the coupling of especially bulky amino acids such as Aib, Tic, ... or in the case of recognized difficult coupling we recommend the replacement of HOBt by HOAt, or the use of other activating agents.

For peptide chemists themselves, Fmoc chemistry ..

Consequently, these reagents are suitable for the coupling of sterically hindered amino acids, thereby ensuring greater success in the synthesis of difficult peptides (16-17).

The greening of peptide synthesis - Green Chemistry …

Reliable methods detecting minute amounts of unreacted amino groups are essential for the monitoring of the coupling reaction. On the other hand the ability of detecting small quantities of Fmoc peptide allows the control of the completion of the Fmoc cleavage.

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